Planning a special date soon? Or getting ready for Valentine’s Day? And have everything handled…except for what to wear? We can help.
When you’re looking for men’s date night outfits, you’ve come to the right place. Our expert Stylists compiled the definitive guide to date-night looks to fit every vibe. From casual-cool to all dressed up, there’s an outfit for every man.
So, let’s get into it! Here’s our Stylists’ top 6 men’s date night outfit ideas for your next special outing.
The Risk Taker
If you’re into trying something new, this is a great look for you. Instead of the typical button-down, a fresh swap is a sweater polo. It’s a trending alternative that’s just as dressed up, but even comfier. And you can still wear it with your trusty jeans. For a nicer occasion like date night a snazzy restaurant, dark-wash or black denim elevate the look with ease.
Another key to the perfect dinner date outfits for men: Have fun with your outer layer. A bomber is always a classic style. Want to try something new? Go for a Harrington jacket: a lightweight waist-length jacket with a zipper and collar. As another option, Stylist Dania suggests, “Grab your favorite leather jacket and pair it with a well-fitted tee, followed by dark indigo jeans and boots.” This is a great outfit combo with the perfect amount of edge.
“Grab your favorite faux leather jacket and pair it with a well-fitted tee.”
The Remarkably Rugged
More of an outdoorsy type? No prob. Here’s a great casual date night outfit for men. Stylist Dania notes, “Get the perfect balance of synchronizing sophistication with a rugged twist.” A plaid shirt is such a great starting point. “Flannel and plaid shirts are the perfect amount of rugged,” says Dania. Wear them on their own, or get some extra styling points by keeping them unbuttoned with a tee or long-sleeve underneath. Add on a fresh pair of white sneaks and you’re ready.
Looking to dress up your rugged look? Try a sleek button-down (totally OK to keep it untucked) paired with a colored pair of jeans, like a brown hue. Finish with a collared tan jacket and matching brown boots. A great tip for putting your look together is to stick with a set color combo. For a rugged look, think earth tones like green, brown, and cream.
“Get the perfect balance of synchronizing sophistication with a rugged twist.” -Dania, Stylist
The Casually Cool
Chill, laidback and easy-going. Sound like you? Here’s a sharp outfit idea that gives off an effortless look and feel. Start with an all-black base—there’s really nothing more effortless than that. We recommend a crisp polo and great-fitting jeans. To bring it up a notch, add a neutral-colored shacket (AKA a shirt-jacket hybrid). It’s a casual yet stylish layer. Then, finish everything off with your favorite pair of sneakers. Keeping them white or neutral will really tie your whole outfit together.
Stylist Dania offers a leveled-up option: “Wear your crisp button down shirt with relaxed jeans for a comfortable yet polished look” and then, “Finish your look off with casual loafers—perfect for casual dinner.” If you want a no-fail best date night outfit for men, this is the one.
“Wear your crisp button down shirt with relaxed jeans for a comfortable yet polished look.” -Stylist Dania
The Perfectly Polished
Let’s say you really feel like stepping it up for your date. Maybe it’s a fancy candlelit dinner you had to reserve three months in advance. Here’s Stylist Dania’s advice for dressing up your look: “Nothing gives a touch of sophistication like a tailored blazer layered over a button-down.” This is a great time to showcase a printed or patterned button-down. Want to stay in your comfort zone? Pick a super-small pattern or a print in your typical go-to color. “Neutral trousers and dress shoes are the perfect way to complete this look,” Dania adds.
If mixing and matching your blazer and trousers seems too daunting, you can always rely on a matching suit. Keep it monochrome to avoid any styling confusion. Go for a light blue button-down, navy blazer and pants with some sleek brown shoes to finish.
“Nothing gives a touch of sophistication like a tailored blazer.” -Dania, Stylist
The Modern Classic
Chinos: a classic for a reason. It’s one of the best ways to start off a date night outfit for men. They’re so easy to dress up or down, and they’re a staple style that should be in your wardrobe. Stylist Dania advises, “Elevate your look for a smart-casual date by wearing a tailored pair of chinos,” then says to pair them “with a button-down shirt layered with a sweater on top.” Finish off your look with some chukka boots.
For a more casual twist, pair your chinos with a crisp white tee and matching sneaks. Then, add your favorite jacket over top to finish off your look. Simple yet effective!
“Elevate your look for a smart-casual date by wearing a tailored pair of chinos.” -Dania, Stylist
The Effortlessly Practical
If there’s not only love in the air but also a slight chill, you’ll want to layer up for your date. It’s also the perfect excuse to drape your jacket over your date’s shoulders if they’re chilly. Very romantic. Stylist Dania notes that the key is, “Mix textures, colors and patterns with different silhouettes to create versatile and functional outfits for any setting.” She adds, “Layer a shirt jacket over your favorite top. This can be a T-shirt, polo, sweater, button-down…you name it!”
You can achieve this with a knit polo, shacket, jeans and tie it together with some sneakers. Want to go full texture? Try this: classic tee, corduroy pants, denim jacket and faux leather boots. Layering up different textures in one look really levels up your outfit.
“Mix textures, colors and patterns with different silhouettes to create versatile and functional outfits for any setting.” -Dania, Stylist
Get date night ready with Stitch Fix
Want to get all the date-night outfits, tips and tricks from your very own Stylist? Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or keep 5+ pieces and get 20% off your entire order. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
